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People Pleasing and Boundaries: When the Rules Stop Working

Aug 18
5 min read
Man floating in an inner tube on the Missouri River near a bridge, caught in a looping river current.
Even rivers have exceptions to the rule. Floating the Missouri River, I found an eddy that kept carrying me in a loop instead of downstream. Sometimes the rule makes perfect sense—until reality gives you a reason to update it.

My mother told me to bring everything off the bed downstairs to get washed.

I needed help.

Because I couldn't carry the mattress downstairs by myself.

To me, this was perfectly logical.

The bed was the frame. The mattress was on the bed. Mom said to bring everything off the bed downstairs.

Therefore: mattress downstairs.

Except, of course, that's not what she meant.

And I sometimes wonder how much of adulthood consists of discovering that we're still trying to carry mattresses downstairs.

When Following the Rule Doesn't Work

You may remember Amelia Bedelia, the children's book character famous for taking instructions literally. She wasn't a particular childhood favorite of mine, but the premise was memorable: Amelia could understand the words and completely miss what someone meant.

I apparently had a little Amelia Bedelia in me.

My mother's instruction contained an implied category: Bring down the bedding we normally wash.

Nobody talks that precisely because human communication relies on context.

I understood the words.

I missed the context.

Other times, the problem is different.

Before starting kindergarten, I needed a shot. My doctor, Dr. Ho, told me:

“Don't move. The more you move, the more it'll hurt.”

What my little-kid brain heard was:

If you don't move, it won't hurt.

So I remained perfectly still.

The shot still hurt.

Dr. Ho hadn't lied. “Moving makes it hurt more” never meant “staying still makes it painless.”

I had added a promise to the rule that nobody actually made.

Then there was football.

We'd been told that if a kickoff went to somebody other than the designated returners, take a knee.

Eventually, one came to me.

I caught it.

I took a knee.

My coach responded:

“Curtis, you could have run with it!”

Apparently, the rule was really intended for the linemen.

That would have been useful information earlier.

This time I hadn't misunderstood anything.

I correctly followed an incomplete rule.

The Rules We Carry Into Adulthood

The childhood versions are funny.

The adult rules can be much more consequential:

Work hard.

Be nice.

Don't be selfish.

Forgive.

Never give up.

Treat people the way you want to be treated.

Set boundaries.

Most of these are good advice.

But eventually life becomes too complicated for the simple version of the rule.

That's especially true with people pleasing and boundaries.

Treating people well is good.

But what if someone exploits your generosity?

Set boundaries.

Okay—but make your boundaries rigid enough and nobody can exploit you because nobody can get close enough to you.

So which rule wins?

The answer requires understanding why the rule exists.

Follow Your Shot—But Why?

Think about an old basketball rule:

Follow your shot.

Why?

If you miss, you might get the rebound.

Why get the rebound?

To regain possession.

Why?

To score.

Why?

To win.

Now we've reached the actual objective.

And suddenly the simple rule isn't absolute anymore.

If following my shot gives us another possession, great.

But if my responsibility is getting back on defense and crashing the basket gives the opponent an easy fast break, following my shot could actually hurt our chances of winning.

The deeper principle isn't “follow your shot.”

It's:

Understand what you're trying to accomplish and choose the action most likely to accomplish it.

Life requires the same upgrade.

People Pleasing and Boundaries

People pleasing rarely starts with a terrible idea.

It often starts with good principles:

Be considerate.

Help people.

Care about other people's feelings.

But eventually:

“I want to be considerate” becomes:

“I'm responsible for everyone else's feelings.”

“I want to help” becomes:

“Saying no makes me selfish.”

“I believe in forgiveness” becomes:

“I have to keep giving someone another chance.”

A good principle has become a rigid rule.

And we can follow it faithfully while becoming exhausted, anxious, resentful, or overwhelmed.

That's when someone tells us to set boundaries.

Also good advice.

But healthy boundaries aren't walls.

Relationships require compromise, vulnerability, generosity, and sometimes sacrifice.

The question isn't simply:

Should I put myself first or other people first?

It's:

What am I trying to create, what is this choice likely to produce, and what will it cost?

Worthwhile Sacrifice vs. Pointless Suffering

Everything meaningful costs something.

We spend time, energy, attention, money, freedom, opportunity, and emotional capacity.

Hopefully those sacrifices produce something worthwhile: connection, meaning, security, love, accomplishment, health, contribution, or joy.

That's why avoiding discomfort isn't always the answer.

Growth can hurt.

Saying no can hurt.

An honest conversation can hurt.

Leaving something unhealthy can hurt.

Working toward something meaningful can require tremendous sacrifice.

The goal isn't necessarily to minimize pain.

It's learning to distinguish worthwhile sacrifice from pointless suffering.

And that requires more than memorizing rules.

It requires understanding cause and effect.

Maybe You Aren't Failing at the Rules

Sometimes people come to counseling because they've tried incredibly hard to do everything “right.”

They worked hard.

They accommodated.

They forgave.

They avoided conflict.

They persevered.

They tried to be good partners, parents, friends, and employees.

And they're still anxious, exhausted, resentful, overwhelmed, or stuck.

They ask:

What am I doing wrong?

Sometimes a better question is:

What rules am I living by—and are they actually producing what they're supposed to produce?

Where did this rule come from?

What was it supposed to accomplish?

What is following it costing me?

What is it producing?

Am I misunderstanding it?

Am I expecting a promise nobody made?

Or am I standing in an open football field holding the ball because someone once told me to take a knee?

Counseling for People Pleasing and Boundaries

At Authentic Wellness & Empowerment, counseling isn't about handing people another list of rules.

Most of us already have plenty.

Counseling can help us examine the beliefs, assumptions, relationship patterns, and experiences influencing our choices—particularly when we're struggling with people pleasing and boundaries, anxiety, perfectionism, overthinking, relationships, stress, or difficult life decisions.

The goal is greater clarity about what's happening, greater courage to make difficult changes, and greater capacity to carry those changes forward.

Sometimes you don't need another rule.

You need a better understanding of the rules you're already living by.

My mother didn't want the mattress downstairs.

Dr. Ho never promised the shot wouldn't hurt.

My football coach apparently didn't want me taking a knee.

And sometimes you shouldn't follow your shot.

Keep the good rules. Keep asking why. And when reality teaches you something new, update the rule.

Struggling With People Pleasing and Boundaries?

If you're struggling with people pleasing and boundaries, overthinking, anxiety, perfectionism, or relationship patterns—and doing everything you're “supposed” to do still isn't working—counseling may help.

Authentic Wellness & Empowerment helps individuals, couples, and families develop the clarity, courage, and capacity to create the lives they want.

Schedule a counseling appointment with Authentic Wellness & Empowerment today.

 
 
 

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